Bis(2-bromoethyl) ether → HCID 54307926, compound

HRID 1981988Notes

Reaction equation

HRID 1981988 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:17](=[O:19])[CH3:18])[C:10]([OH:16])=[CH:11][CH:12]=2)[CH:7]=1.[H-].[Na+].[Br:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28]Br>CN(C)C=O>[CH3:1][O:2][C:3](=[O:20])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:17](=[O:19])[CH3:18])[C:10]([O:16][CH2:28][CH2:27][O:26][CH2:25][CH2:24][Br:23])=[CH:11][CH:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydrideHCID 13504771HCID 13504771, compound

Product 1

HCID 54307926HCID 54307926, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, 2 g of [[8-acetyl-7-hydroxy-2-naphthalenyl]oxy]acetic acid methyl ester was added to a suspension of 0.32 g of 60% sodium hydride in 30 ml of anhydrous dimethylformamide. The mixture was stirred at room temperature for 30 minutes and then 8.5 g of bis-(2-bromoethyl)ether was added and the mixture was stirred at room temperature for 20 hours. The solvent was removed and residual oil was purified by high pressure liquid chromatography using 7% ethyl acetate-toluene to yield 2.4 g (77%) of [[8-acetyl-7-[2-(2-bromoethoxy)ethoxy]-2-naphthalenyl]oxy]acetic acid methyl ester as an oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hours
  2. customThe solvent was removed
  3. customresidual oil was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-d8d68045601e4863884127f8ab0d1fd5
Source dataset
uspto-grants-1986_06
Patent number
US04594442

Reaction notes

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